Synthesis of O-(2-O-sulfo-α-L-idopyranosyluronic acid)-(1 → 3)-2- acetamido-2-deoxy-4-O-sulfo-D-galactopyranose trisodium salt, a disaccharide fragment of dermatan sulfate

Carbohydrate Research

Volumn 305, Issue 2, 1997, Pages 181-191

  Rochepeau Jobron, Laurence ^a,b   Jacquinet, Jean Claude ^a,b  

^a UNIVERSITÉ D'ORLÉANS   (France)

^b XVIIIth Intl Carbohydrate Symposium   (Italy)

Author keywords

D Galactosamine; Dermatan sulfate; Disaccharide; L Iduronic acid; Synthesis

Indexed keywords

DERMATAN SULFATE DERIVATIVE; DISACCHARIDE;

ARTICLE; CARBOHYDRATE ANALYSIS; CARBOHYDRATE SYNTHESIS; POLYMERIZATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS;

EID: 0031433115     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0008-6215(97)10017-9     Document Type: Article

References (32)

1. [1] K. Meyer and E. Chaffee, J. Biol. Chem., 138 (1941) 491-499.
2. [2] C.A. Poblacion and Y.M. Michelacci, Carbohydr. Res., 147 (1986) 87-100.
3. [3] D.M. Tollefsen, C.A. Pestka, and W.J. Monafo, J. Biol. Chem., 258 (1983) 6713-6716.
4. [4] M.M. Maimone and D.M. Tollefsen, J. Biol. Chem., 265 (1990) 18263-18271.
5. [5] G. Mascellani, L. Liverani, A. Prete, G.L. Bergonzoni, P. Bianchini, L. Silvestro, G. Torri, A. Bisio, M. Guerrini, and B. Casu, J. Carbohydr. Chem., 14 (1995) 1165-1171.
6. [6] K. Bezouska, C.T. Yuen, J. O'Brien, R.A. Childs, W. Chai, A.M. Lawson, K. Drbal, A. Fiserova, M. Pospisil, and T. Feizi, Nature, 372 (1994) 150-157.
7. [7] J.-C. Jacquinet and P. Sinaÿ, Carbohydr. Res., 159 (1987) 229-253.
8. [8] A. Marra, X. Dong, M. Petitou, and P. Sinaÿ, Carbohydr. Res., 195 (1989) 39-50.
9. [9] F. Goto and T. Ogawa, Bioorg. Med. Chem. Lett., 4 (1994) 619-624.
10. [10] G. Blatter and J.-C. Jacquinet, Carbohydr. Res., 288 (1996) 109-125 and references cited therein.
11. [11] R.U. Lemieux and R.M. Ratcliffe, Can. J. Chem., 57 (1979) 1244-1251.
12. [12] C. Coutant and J.-C. Jacquinet, J. Chem. Soc., Perkin Trans. I, (1995) 1573-1581.
13. [13] F. Belot and J.-C. Jacquinet, Carbohydr. Res., 290 (1996) 79-86.
14. [14] P.H. Gross, F. du Bois, and R.W. Jeanloz, Carbohydr. Res., 4 (1967) 244-248.
15. [15] L. Lay, F. Nicotra, L. Panza, G. Russo, and E. Adobati, Helv. Chim. Acta, 77 (1994) 509-514.
16. [16] M.L. Shulman and A.Ya. Khorlin, Carbohydr. Res., 27 (1973) 141-147.
17. [17] H.M. Flowers and D. Shapiro, J. Org. Chem., 30 (1965) 2041-2043.
18. [18] P.H. Gross and R.W. Jeanloz, J. Org. Chem., 32 (1967) 2759-2763.
19. [19] K.L. Matta, E.A. Johnson, and J.J. Barlow, Carbohydr. Res., 26 (1973) 215-218.
20. [20] J.-C. Jacquinet, M. Petitou, P. Duchaussoy, I. Lederman, J. Choay, G. Torri, and P. Sinaÿ, Carbohydr. Res., 130 (1984) 221-241.
21. [21] G. Catelani, F. Colonna, and A. Marra, Carbohydr. Res., 182 (1988) 297-300.
22. [22] S.S. Rana and K.L. Matta, Carbohydr. Res., 116 (1983) 71-81.
23. [23] R.U. Lemieux and H. Driguez. J. Am. Chem. Soc., 97 (1975) 4069-4075.
24. [24] L. Rochepeau-Jobron and J.-C. Jacquinet, Carbohydr. Res., (1997) in press (CAR 916).
25. [25] G. Blatter, J.-M. Beau, and J.-C. Jacquinet, Carbohydr. Res., 260 (1994) 189-202.
26. [26] H. Paulsen and O. Lockhoff, Chem. Ber., 114 (1981) 3102-3114.
27. [27] C. Tabeur, F. Machetto, J.-M. Mallet, P. Duchaussoy, M. Petitou, and P. Sinaÿ, Carbohydr. Res., 281 (1996) 253-276.
28. [28] V.J. Patil, Tetrahedron Lett., 37 (1996) 1481-1484.
29. [29] T. Iversen and D.R. Bundle, J. Chem. Soc. Chem. Commun., (1981) 1240-1241.
30. [30] G. Jaurand, C. Tabeur, and M. Petitou, Carbohydr. Res., 255 (1994) 295-301.
31. [31] H. Lucas, J.E.M. Basten, T.G. van Dinther, D.G. Meuleman, S.F. van Aelst, and C.A.A. van Boeckel, Tetrahedron, 46 (1990) 8207-8228.
32. [32] J.-C. Jacquinet, Carbohydr. Res., 199 (1990) 153-181 and references cited therein.